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Application of ring A dioxane flavonolignan in preparing medicaments for resisting hepatitis B viruses (HBV)

A technology of flavonoid lignan and dioxane couple, which is applied in the direction of antiviral agents, medical preparations containing active ingredients, and pharmaceutical formulas, can solve the problems that new uses have not been effectively developed, and achieve the benefits of large-scale production, The prospect of industrialization is clear, the effect of large-scale production of energy saving and emission reduction

Inactive Publication Date: 2010-09-15
DALI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] Although the flavonoid lignans represented by silibinin have the above-mentioned antioxidant effects, there are relatively few literatures on their antiviral treatment. The flavonoid lignans treat DNA virus infection especially Its new use for anti-hepatitis B virus (including inhibition of hepatitis B e antigen HBeAg or inhibition of HBV DNA replication) has not been effectively developed, so the active compound in the field of anti-hepatitis B virus is searched from flavonoid lignans, that is, flavonoid lignans Structural engineering for anti-DNA viroid activity is a new field

Method used

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  • Application of ring A dioxane flavonolignan in preparing medicaments for resisting hepatitis B viruses (HBV)
  • Application of ring A dioxane flavonolignan in preparing medicaments for resisting hepatitis B viruses (HBV)
  • Application of ring A dioxane flavonolignan in preparing medicaments for resisting hepatitis B viruses (HBV)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: Formula (1) compound (±)-trans-6-hydroxyl-2-hydroxymethyl-3-(4-hydroxyphenyl)-9-phenyl-2,3-dihydro-[1,4]diox Preparation instruments and reagents of hexacyclo[2,3-h]benzopyran-7-one:

[0029] The ultraviolet spectrum was measured with a Shimadzu UV-240 ultraviolet spectrophotometer; the hydrogen nuclear magnetic resonance spectrum 1 H-NMR is measured by INOVA type superconducting nuclear magnetic resonance spectrometer (VARIAN INOVA-400MHz) (tetramethylsilyl ether TMS is the internal standard); (100-200, 200-300 and 300-400 mesh) and silica gel GF254 (10-40 mesh) for thin layer chromatography are all produced by Qingdao Ocean Chemical Factory; all reagents used are analytically pure, and the boiling range of petroleum ether is 60 -90°C; thin-layer preparative chromatography (PTLC) uses aluminum foil silica gel plates from Merck; column chromatography uses dextran gel Sephadex LH-20 from Amersham Pharmacia Biotech AB in Sweden; reverse-phase silica gel RP-18...

Embodiment 2

[0031] Example 2: Inhibitory effect of compound of formula (1) on hepatitis B e antigen (HBeAg) secreted by HepG2.2.15 cells

[0032] 2.1 Cell culture:

[0033]HepG2.2.15 cells were cultured in DMEM medium containing 10% inactivated fetal bovine serum, 100 U / ml penicillin and 100 U / ml streptomycin, 100 μg / ml G418 at 37°C, 5% CO 2 , cultured in an incubator with 100% relative humidity.

[0034] 2.2 The inhibitory effect of compound (1) on the growth of HepG2.2.15 cells was determined by MTT method:

[0035] Take the HepG2.2.15 cells in the logarithmic growth phase, and dilute the cells to 1×10 with medium 5 cells / ml, seeded in 96-well cell culture plate, 100 μl per well, at 37°C, 5% CO 2 After 24 hours in an incubator with 100% relative humidity, add compound (1) diluted with medium, the concentration is 1000 μg / ml, 200 μg / ml, 40 μg / ml and 8 μg / ml, 200 μg / ml in each well microliter, each concentration was set up in triplicate, placed at 37°C, 5% CO 2 , cultivated in an i...

Embodiment 3

[0042] Example 3: Inhibition of the replication of hepatitis B virus deoxyribonucleic acid (HBV DNA) secreted by the compound of formula (1) to HepG2.2.15 cells

[0043] 3.1 Cell culture: the method is the same as in Example 2.

[0044] 3.2 The inhibitory effect of the flavonoid lignan compound represented by formula (1) on the growth of HepG2.2.15 cells was determined by MTT method: the method is the same as that in Example 2.

[0045] 3.3 The flavonoid lignan compounds shown in the assay formula (1) inhibit the replication of hepatitis B virus deoxyribonucleic acid (HBV DNA): get the HepG2.2.15 cells in the logarithmic growth phase, and use the culture medium to dilute the cells to 1 ×10 5 cells / ml, seeded in 96-well cell culture plate, 100 μl per well, at 37°C, 5% CO 2 After cultivating in an incubator with 100% relative humidity for 24 hours, add the flavonoid lignan compound shown in the formula (1) diluted with the medium, the concentration is respectively 100 microg...

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Abstract

The invention relates to application of ring A dioxane flavonolignan in preparing medicaments for resisting hepatitis B viruses (HBV), in particular to application of ring A dioxane coupling type flavone lignan or a pharmaceutically acceptable salt thereof in preparing medicaments for clearing away hepatitis B e antigen (HBeAg), suppressing the HBV DNA replication and treating HBV infection diseases. The flavonolignan has certain activity on resisting the HBeAg, and the intensity of the flavonolignan for clearing away the HBeAg is higher than that of Lamivudine which is a positive control and close to that of 10,000 units / milliliter of alpha-interferon. Meanwhile, the suppression ratio of the compound to the HBV DNA replication is higher than 80 percent in the presence of a concentration of 100 micrograms / milliliter. The pharmacodynamical results indicate that the flavonolignan or the pharmaceutically acceptable salt thereof can be expected to be used for preparing the medicaments for clearing away the HBeAg, suppressing the HBV DNA replication and treating the HBV infection diseases.

Description

technical field [0001] The present invention relates to the technical field of medicine, in particular, the present invention relates to a flavonoid lignan compound having a dioxane coupling structure on an A ring represented by formula (1) or a pharmaceutically acceptable salt thereof for preparing hepatitis B-clearing e antigen, inhibiting hepatitis B virus deoxyribonucleic acid HBVDNA replication, and the use of drugs for treating hepatitis B virus. The flavonoid lignans have been found to have a certain inhibitory activity of hepatitis B virus core antigen HBeAg through pharmacodynamic tests, and its HBeAg clearance intensity At a concentration of 100 micrograms / ml, it is higher than the positive control lamivudine, and close to 10,000 units / ml of α-interferon; at the same time, at 100 micrograms / ml, the compound shows an inhibition rate greater than 80% for HBV DNA. The above pharmacodynamic results show that the A-ring dioxane-coupled flavonoid lignans or their pharmaceu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/357A61P31/20
Inventor 彭芳丁红霞徐路龚景旭张礼和巫秀美赵昱郝小江
Owner DALI UNIV
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